Synthesis of amphiphilic hydantoin-based universal peptidomimetics as antibiotic agents
Alessio M Caramiello1, Maria Cristina Bellucci2, Emerenziana Ottaviano3
1Department of Chemistry, Materials and Chemical Engineering "Giulio Natta", Politecnico di Milano, via Mancinelli 7, 20131 Milano, Italy. alessandro.volonterio@polimi.it.
Abstract:
Three model hydantoin-based universal peptidomimetics were designed and synthetized. Their preferred amphiphilic β-turn conformation was assessed using molecular modeling and NMR experiments, and their antibacterial activity was tested against Gram-positive and Gram-negative bacteria strains, which demonstrated that these compounds could be a captivating class of antibiotics to fight emergent drug resistance.
Related Concept Videos
Peptidoglycan Synthesis
Amides to Carboxylic Acids: Hydrolysis
Acid-catalyzed hydrolysis:
Hydrolysis of amides under acidic conditions yields carboxylic acids. Since the reaction occurs slowly, hydrolysis requires the conditions of heat.
The mechanism begins with the protonation of the carbonyl oxygen by the acid catalyst. The protonation makes the amide carbonyl carbon more...
Preparation of Amides
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
Combined Effects of Drugs: Synergism
Such synergistic combinations...


